EP3250648B1 - Compositions d'encre électrostatique - Google Patents

Compositions d'encre électrostatique Download PDF

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Publication number
EP3250648B1
EP3250648B1 EP15701977.9A EP15701977A EP3250648B1 EP 3250648 B1 EP3250648 B1 EP 3250648B1 EP 15701977 A EP15701977 A EP 15701977A EP 3250648 B1 EP3250648 B1 EP 3250648B1
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EP
European Patent Office
Prior art keywords
examples
pigment
ink composition
electrostatic ink
cyan
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EP15701977.9A
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German (de)
English (en)
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EP3250648A1 (fr
Inventor
Tal ROSENTHAL
Marc Klein
Albert Teishev
Gil Bar-Haim
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HP Indigo BV
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HP Indigo BV
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/085—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex substituting the central metal atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/52—Electrically conductive inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/12—Developers with toner particles in liquid developer mixtures
    • G03G9/122—Developers with toner particles in liquid developer mixtures characterised by the colouring agents
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/12—Developers with toner particles in liquid developer mixtures
    • G03G9/135—Developers with toner particles in liquid developer mixtures characterised by stabiliser or charge-controlling agents
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/12—Developers with toner particles in liquid developer mixtures
    • G03G9/135—Developers with toner particles in liquid developer mixtures characterised by stabiliser or charge-controlling agents
    • G03G9/1355—Ionic, organic compounds

Definitions

  • Electrophotographic printing processes typically involve creating an image on a photoconductive surface, applying an ink having charged particles to the photoconductive surface, such that they selectively bind to the image, and then transferring the charged particles in the form of the image to a print substrate.
  • the photoconductive surface is typically on a cylinder and is often termed a photo imaging plate (PIP).
  • PIP photo imaging plate
  • the photoconductive surface is selectively charged with a latent electrostatic image having image and background areas with different potentials.
  • an electrostatic ink composition including charged toner particles in a liquid carrier can be brought into contact with the selectively charged photoconductive surface.
  • the charged toner particles adhere to the image areas of the latent image while the background areas remain clean.
  • the image is then transferred to a print substrate (e.g. paper) directly or, more commonly, by being first transferred to an intermediate transfer member, which can be a soft swelling blanket, which is often heated to fuse the solid image and evaporate the liquid carrier, and then to the print substrate.
  • liquid carrier refers to the fluid in which the polymer resin, pigment, charge directors and/or other additives can be dispersed to form a liquid electrostatic ink or electrophotographic ink.
  • Liquid carriers can include a mixture of a variety of different agents, such as surfactants, co-solvents, viscosity modifiers, and/or other possible ingredients.
  • electrostatic ink composition generally refers to an ink composition, which may be in liquid form, that is typically suitable for use in an electrostatic printing process, sometimes termed an electrophotographic printing process.
  • the electrostatic ink composition may include chargeable particles of the resin and the pigment dispersed in a liquid carrier, which may be as described herein.
  • co-polymer refers to a polymer that is polymerized from at least two monomers.
  • a certain monomer may be described herein as constituting a certain weight percentage of a polymer. This indicates that the repeating units formed from the said monomer in the polymer constitute said weight percentage of the polymer.
  • electrostatic(ally) printing or “electrophotographic(ally) printing” generally refers to the process that provides an image that is transferred from a photo imaging substrate or plate either directly or indirectly via an intermediate transfer member to a print substrate, e.g. a paper substrate. As such, the image is not substantially absorbed into the photo imaging substrate or plate on which it is applied.
  • electrostatic printers or “electrostatic printers” generally refer to those printers capable of performing electrophotographic printing or electrostatic printing, as described above.
  • Liquid electrophotographic printing is a specific type of electrophotographic printing where a liquid ink is employed in the electrophotographic process rather than a powder toner.
  • An electrostatic printing process may involve subjecting the electrophotographic ink composition to an electric field, e.g. an electric field having a field strength of 1000 V/cm or more, in some examples 1000 V/mm or more.
  • the term "about” is used to provide flexibility to a numerical range endpoint by providing that a given value may be a little above or a little below the endpoint.
  • the degree of flexibility of this term can be dictated by the particular variable and would be within the knowledge of those skilled in the art to determine based on experience and the associated description herein.
  • the present disclosure relates to a cyan electrostatic ink composition.
  • the cyan electrostatic ink composition may comprise: a cyan pigment, a basic dispersant, a phthalocyanine having acid groups, a resin and a charge director.
  • the present disclosure relates a method of producing a cyan electrostatic ink composition.
  • the method may comprise: combining a cyan pigment, a basic dispersant and a phthalocyanine having acid groups, a resin, and a charge director to form the electrostatic ink composition.
  • the present disclosure relates a print medium, having printed thereon a cyan electrostatic ink composition.
  • the cyan electrostatic ink composition printed on the print medium may comprise a cyan pigment, a basic dispersant, a phthalocyanine having acid groups, and a resin.
  • the cyan pigment is phthalocyanine pigment, different from the phthalocyanine having acid groups.
  • the cyan pigment may lack acid side groups.
  • the cyan pigment is selected from pigment blue 15:1, pigment blue 15:2, pigment blue 15:3, pigment blue 15:4, pigment blue 15:5, pigment blue 15:6, pigment green 7 and pigment blue 36.
  • the cyan pigment is selected from pigment blue 15:1, pigment blue 15:2, pigment blue 15:3, pigment blue 15:4, pigment blue 15:5 and pigment blue 15:6.
  • the cyan pigment comprises a first pigment selected from pigment blue 15:1, pigment blue 15:2, pigment blue 15:3, pigment blue 15:4, pigment blue 15:5, pigment blue 15:6 and a second pigment selected from pigment green 7 and pigment blue 36, and, in some examples, the first pigment is present in the electrostatic ink composition in a greater amount than the second pigment.
  • the cyan pigment may constitute from 1 wt% to 30 wt% of the solids of the electrostatic ink composition, in some examples from 5 wt% to 25 wt% of the solids of the electrostatic ink composition, in some examples from 10 wt% to 20 wt% of the solids of the electrostatic ink composition, in some examples from 10 wt% to 15 wt% of the solids of the electrostatic ink composition, in some examples from 15 wt% to 20wt% of the solids of the electrostatic ink composition.
  • the phthalocyanine having acid groups may of formula (I) wherein R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , R 4' , R 1" , R 2" , R 3" , R 4" , R 1"' , R 2" , R 3"' , R 4'” are each independently selected from H and an acidic group, with at least one of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3 , R 4' , R 1" , R 2" , R 3" , R 4" , R 1"' , R 2"' , R 3"' , R 4'" being an acidic group.
  • R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , R 4' , R 1'" , R 2" , R 3" , R 4" , R 1"' , R 2"' , R 3"' , R 4'” is an acidic group.
  • R 1" , R 2" , R 3" , R 4" , R 1"' , R 2"' , R 3"' , R 4'" is an acidic group.
  • At least four of R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , R 4' , R 1" , R 2" , R 3" , R 4" , R 1"' , R 2"' , R 3"' , R 4'” is an acidic group.
  • the acidic group may be selected from a Bronsted acid group and a Lewis acid group.
  • the acidic group may be selected from a carboxyl group, a sulfate acid group, a sulfonic acid group, phosphate acid group, nitric acid group, boric acid group, chromic Bronsted acid group and a Lewis acid group.
  • the acidic group e.g.
  • a carboxyl group, a sulfate acid group, a sulfonic acid group, phosphate acid group, nitric acid group, boric acid group, chromic Bronsted acid group and a Lewis acid group may be linked to the phthalocyanine ring by a linker group.
  • the organic linker group may comprise or be a hydrocarbon group.
  • the organic linker group may comprise from 1 to 10 carbon atoms, in some examples 1 to 5 carbon atoms, in some examples 1 to 3 carbon atoms.
  • the organic linker group may comprise or be a group selected from optionally substituted alkylene, optionally substituted alkenylene and optionally substituted alkynylene.
  • the group selected from optionally substituted alkylene, optionally substituted alkenylene and optionally substituted alkynylene may comprise from 1 to 10 carbon atoms, in some examples 1 to 5 carbon atoms, in some examples 1 to 3 carbon atoms, excluding any substituents that may be present.
  • the substituent(s) on a substituted group may (each independently) be selected from alkyl, alkenyl, alkynyl, -O-alkyl, -O-alkanoyl, halogen, heterocyclyl, alkoxycarbonyl, hydroxy, mercapto, nitro, acyloxy, hydroxy, thiol, acyl, cycloalkyl, cycloalkenyl, substituted alkyl, substituted alkoxy, substituted alkenyl, substituted alkynyl, substituted cycloalkyl, substituted cycloalkenyl, amino, substituted amino, aminoacyl, acylamino, alkaryl, aryl, aryloxy, azido, carboxy, carboxyalkyl, cyano, nitro, heteroaryl, heteroaryloxy, heterocyclic, heterocyclooxy, aminoacyloxy, oxyacylamino, thioalkoxy, substituted thioalkoxy,
  • R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , R 4' , R 1" , R 2" , R 3" , R 4" , R 1"' , R 2"' , R 3"' , R 4'" are each independently selected from H and an acidic group selected from a Bronsted acid group and a Lewis acid group.
  • R 1 , R 2 , R 3 , R 4 , R 1' , R 2' , R 3' , R 4' , R 1" , R 2" , R 3" , R 4" , R 1"' , R 2"' , R 3"' , R 4'” are each independently selected from H and an acidic group selected from a carboxyl group, a sulfate acid group, a sulfonic acid group, phosphate acid group, nitric acid group, boric acid group, chromic Bronsted acid group and a Lewis acid group, which may be, in some examples, linked to the phthalocyanine ring by a linker group.
  • R 3 , R 3' , R 3" , and R 3"' are each an acidic group selected from a carboxyl group, a sulfate acid group, a sulfonic acid group, phosphate acid group, nitric acid group, boric acid group, chromic Bronsted acid group and a Lewis acid group, which may be, in some examples, linked to the phthalocyanine ring by a linker group, and R 1 , R 2 , R 4 , R 1' , R 2' , R 4' , R 1" , R 2" , R 4" , R 1' , R 2"' , R 4'" are each H.
  • the wt:wt ratio of cyan pigment:phthalocyanine having acid groups is from 100:1 to 1:100, in some examples from 50:1 to 1:1, in some examples from 40:1 to 2:1, in some examples from 20:1 to 10:3.
  • the wt:wt ratio of cyan pigment:phthalocyanine having acid groups is from 5:1 to 100:1, in some examples from 20:1 to 50:1, in some examples 25:1 to 35:1.
  • the method involves using and/or the electrostatic ink composition includes a basic dispersant, and in some examples the dispersant is or comprises a polymeric dispersant or a surfactant. In some examples, the dispersant is or comprises an electrostatic dispersant or a steric dispersant, or both an electrostatic and a steric dispersant.
  • a polymeric dispersant is a polymeric material having an anchor group capable of being absorbed on to the surface of a particle in a colloidal system and polymeric chains giving steric stabilisation, so as to hold the particles apart.
  • Polymeric dispersants are two-component structures, comprising an anchor group (providing strong adsorption onto the pigment surface by single-point or multi-point anchoring) and one or more polymeric chain(s) (attached to the anchoring group to provide steric stabilization).
  • the dispersant may comprise a polymeric dispersant comprising:
  • the polymeric dispersant is in suspension or dissolved in a solvent, in some examples the dispersant comprises greater than 50 wt% polymeric dispersant, in some examples the dispersant comprises greater than 60 wt% polymeric dispersant, in some examples the dispersant comprises greater than 70 wt% dispersant, in some examples the dispersant comprises greater than 80 wt% polymeric dispersant, in some examples the dispersant comprises greater than 90 wt% polymeric dispersant.
  • the solvent may be an organic solvent, in some examples a deeply hydrogenated solvent, in some examples a solvent which consists essentially of C 9 -C 11 paraffins and naphthenes.
  • the dispersant may consist of, or consist essentially of, polymeric dispersant.
  • the polymeric dispersant is a basic polymeric dispersant.
  • the polymeric dispersant is a basic dispersant, and comprises a basic anchor group, e.g. an amine group.
  • each polymeric dispersant molecule comprises a multi amine anchor group or a single amine anchor group, in some examples each polymeric dispersant molecular comprises a multi amine anchor group.
  • the polymeric dispersant comprises polyolefin amide alkeneamine.
  • each polymeric dispersant molecule comprises one polymer chain or a plurality of polymer chains. In some examples, each polymeric dispersant molecule comprises one polymer chain having a single anchor group, for example an amine group. In some examples, each polymeric dispersant molecule comprises one polymer chain having a plurality of anchor groups, for example a plurality of amine groups. In some examples, the polymer chain has acidic side groups.
  • the polymeric dispersant comprises a co-polymer. In some examples, the polymeric dispersant comprises a block co-polymer having multiple anchor groups, for example an ABA block co-polymer or a BAB block co-polymer or a random copolymer. In some examples, the polymeric dispersant comprises a comb co-polymer.
  • Basic polymeric dispersants include SOLSPERSE® 11200, SOLSPERSE® 13300; the SOLPLUS® series, by the same manufacturer (e.g., SOLPLUS® K500).
  • Other polymeric dispersants that can be used as or with the dispersants described herein include others in the SOLSPERSE® series manufactured by Lubrizol Corp., Wickliffe, OH (e.g., SOLSPERSE® 3000, SOLSPERSE® 8000, SOLSPERSE® 9000, SOLSPERSE® 13840, SOLSPERSE® 16000, SOLSPERSE® 17000, SOLSPERSE® 18000, SOLSPERSE® 19000, SOLSPERSE® 20000, SOLSPERSE® 21000, SOLSPERSE® 27000, or SOLSPERSE® 43000); various dispersants manufactured by BYKchemie, Gmbh, Germany, (e.g., DISPERBYK® 106, DISPERBYK® 110, DISPERBYK® 163, DIS
  • the basic dispersant is or comprises a succinimide.
  • the succinimide may be linked, e.g. via a hydrocarbon-containing linker group, to an amine group.
  • the dispersant comprises a polyisobutylene succinimide having a head group comprising an amine.
  • the dispersant is of formula (II)
  • the dispersant is of formula (II), wherein R a is of formula (III), R b is H and R c is of formula (IV).
  • the dispersant is of formula (II), wherein R a is of formula (III), wherein L is -CH 2 -, R b is H and R c is of formula (IV), whererin m is 1, q is 0 to 10, in some examples 1 to 10, in some examples 1 to 5, o is 1, p is 1 and r is 1.
  • the dispersant is or comprises polyisobutylene succimide polyethylene amine non ionic dispersant.
  • the dispersant is or comprises a dispersant selected from Solperse® J560, Lubrizol® 6406, and Lubrizol 2153. In some examples, the dispersant is or comprises a dispersant selected from OLOA® 11000, OLOA® 371, OLOA® 1200, and OLOA® 15500 with a succinic anhydride chemistry, all of which are available from Chevron Oronite.
  • the dispersant is or comprises an alkyl succimide amido salt, in some examples a polyisobutylene succimide amido salt, in some examples an alkyl succimide amido amino salt, in some examples polyisobutylene succimide amido ammonium salt, and in some examples the polyisobutylene succimide amido ammonium salt comprises a plurality of amido and/or ammonium groups, and in some examples the polyisobutylene succimide amido ammonium salt comprises at least one branched group, e.g. a branched alkyl group, and a plurality of amido and/or ammonium groups, which may be attached, directly or indirectly to the at least one branched group.
  • the dispersant is or comprises OS 13309, which is available from Lubrizol Corporation.
  • the dispersant is a basic dispersant having a total base number (TBN) of at least 5 mgKOH/gr material, in some examples a TBN of at least 10 mgKOH/gr material, in some examples a TBN of at least 20 mgKOH/gr material, in some examples a TBN of at least 30 mgKOH/gr material, in some examples from 5 mgKOH/gr material to 150 mgKOH/gr material, in some examples from 5 mgKOH/gr material to 150 mgKOH/gr material, in some examples from 20 mgKOH/gr material to 140 mgKOH/gr material, in some examples from 5 mgKOH/gr material to 50 mgKOH/gr material, in some examples from 10 mgKOH/gr material to 30 mgKOH/gr material, in some examples from 15 mgKOH/gr material to 25 mgKOH/gr material, in some examples from 15 mgKOH/gr material to 20 mgKOH/gr material.
  • TBN total base number
  • the dispersant is a basic dispersant having a total base number (TBN) of at least 5 mgKOH/gr material, in some examples a TBN of at least 10 mgKOH/gr material, in some examples a TBN of at least 20 mgKOH/gr material, in some examples a TBN of at least 30 mgKOH/gr material, in some examples a TBN of at least 50 mgKOH/gr material, in some examples a TBN of at least 100 mgKOH/gr material, in some examples a TBN of from 5 mgKOH/gr material to 500 mgKOH/gr material, in some examples a TBN of from 100 mgKOH/gr material to 500 mgKOH/gr material, in some examples a TBN of from 200 mgKOH/gr material to 400 mgKOH/gr material.
  • TBN total base number
  • the dispersant is a basic dispersant having a total base number (TBN) of from 30 mgKOH/gr material to 60 mgKOH/gr material, in some examples from 35 mgKOH/gr material to 55 mgKOH/gr material, in some examples about 45 mgKOH/gr material.
  • TBN total base number
  • the dispersant is a basic dispersant having a total base number (TBN) of from 20 mgKOH/gr material to 120 mgKOH/gr material, in some examples from 50 mgKOH/gr material to 90 mgKOH/gr material, in some examples about 90 mgKOH/gr material.
  • TBN total base number
  • the dispersant is a basic dispersant having a total base number (TBN) of from 20 mgKOH/gr material to 120 mgKOH/gr material, in some examples from 50 mgKOH/gr material to 100 mgKOH/gr material, in some examples about 60 mgKOH/gr material to 100 mgKOH/gr material, in some examples about 70 mgKOH/gr material to 80 mgKOH/gr material.
  • TBN total base number
  • the dispersant is a basic dispersant having a total base number (TBN) of at least 100 mgKOH/gr material, in some examples from 100 mgKOH/gr material to 140 mgKOH/gr material, in some examples from 100 mgKOH/gr material to 140 mgKOH/gr material, in some examples from 110 mgKOH/gr material to 130 mgKOH/gr material, in some examples from 115 mgKOH/gr material to 120 mgKOH/gr material.
  • TBN total base number
  • Total base number (TBN), sometimes simply referred to as base number, may be determined using standard techniques, including, those laid out in ASTM Designation D4739 - 08, such as Test Method D2896, Test Method D4739, and ASTM Designation D974 - 08, with Test Method D2896 being used if any discrepancy is shown between test methods, and unless otherwise stated, the test method(s) will be the most recently published at the time of filing this patent application.
  • "mgKOH/gr material” indicates "mgKOH per gram of dispersant”.
  • the measurement of TBN of the dispersant can either be on the pure dispersant, or a dispersant in a hydrocarbon liquid, such 60 wt% dispersant in white spirit, e.g. dearomatized white spirit, and then adjusted as if it had been measured on the pure dispersant.
  • the dispersant which may comprise a succinimide, which may be as described above, has a molecular weight (MW) of from 500 Daltons to 10,000 Daltons, in some examples a MW of from 1000 to 6,000 Daltons, in some examples a MW of from 1000 to 6,000 Daltons, in some examples a MW of from 1000 to 5000 Daltons, in some examples a MW of from 2000 to 4000 Daltons, in some examples a MW of about 3000 Daltons, or in some examples a MW of from 500 to 3000 Daltons, in some examples a MW of from 1000 to 2000 Daltons, in some examples a MW of from 1200 to 1800 Daltons, in some examples a MW of from 1300 to 1500 Daltons, in some examples a MW of 1400 Daltons, or in some examples a MW of from 500 to 3000 Daltons, in some examples a MW of from 1000 to 2000 Daltons, in some examples a MW of from 1200 to 2300 Daltons, in some examples a
  • the dispersant comprises an ester of an optionally substituted fatty acid, in some examples an ester of an optionally substituted hydroxy fatty acid.
  • a fatty acid may be defined as a carboxyl group covalently bonded to a hydrocarbon chain (e.g. a C12 to C22 carbon chain), which may be saturated or unsaturated, and a hydroxy fatty acid is one in which at least one carbon of the hydrocarbon chain of the fatty acid is substituted with a hydroxyl group.
  • the dispersant comprises an ester of an hydroxy fatty acid (the carboxyl group being esterified) in which the hydroxyl group has a substituent thereon, and the substituent may be selected from an optionally substituted alkyl ester (e.g. C1 to C6, e.g. C2 to C4, e.g. C3) or an optionally substituted alkyl amide, wherein the substituent (if present) of the alkyl of the optionally substituted alkyl ester or optionally substituted alkyl amide is a salt, e.g. a trimethyl ammonium salt.
  • an optionally substituted alkyl ester e.g. C1 to C6, e.g. C2 to C4, e.g. C3
  • an optionally substituted alkyl amide wherein the substituent (if present) of the alkyl of the optionally substituted alkyl ester or optionally substituted alkyl amide is a salt, e.g. a trimethyl ammoni
  • the dispersant which may be an oligomeric dispersant, comprises a saturated or unsaturated ricinoleic acid ester capped with a propyl amide terminus connected to tri methyl ammonium salt.
  • the dispersant is or comprises Solplus® K500, available from Lubrizol.
  • the % AOWP (the percentage agent on the weight of pigment) is the number of grams of dispersant per 100g of pigment.
  • the %AOWP of the dispersion is from 1% to 70%, in some examples from 1% to 60%, in some examples from 5% to 55%, in some examples from 10% to 50%, in some examples from 10% to 40%, in some examples from 10% to 30%, in some examples from 15% to 25%, in some examples about 20 %.
  • the dispersant may constitute from 0.1 wt% to 12 wt % of the electrostatic ink composition, in some examples 0.5 wt% to 6 wt% the electrostatic ink composition, in some examples 1 wt% to 6 wt% of the solids of the electrostatic ink composition, in some examples 2 wt% to 4 wt% of the solids of the electrostatic ink composition.
  • the method may involve using and/or the electrostatic ink composition may further include a liquid carrier.
  • the mixing of the pigment, the dispersant and the phthalocyanine having acid groups is carried out in a liquid carrier (i.e. the pigment and dispersant are mixed in a liquid carrier) and/or the grinding of the pigment dispersion and the resin is carried out in a liquid carrier (i.e. the pigment dispersion and the resin is ground in the presence of a liquid carrier).
  • particles including the resin, the pigment and the dispersant may be dispersed in the liquid carrier.
  • the liquid carrier can include or be a hydrocarbon, silicone oil, vegetable oil, etc.
  • the liquid carrier can include, but is not limited to, an insulating, non-polar, non-aqueous liquid that can be used as a medium for toner particles, i.e. the chargeable particles including the resin and, in some examples, a pigment.
  • the liquid carrier can include compounds that have a resistivity in excess of about 10 9 ohm-cm.
  • the liquid carrier may have a dielectric constant below about 5, in some examples below about 3.
  • the liquid carrier can include, but is not limited to, hydrocarbons.
  • the hydrocarbon can include, but is not limited to, an aliphatic hydrocarbon, an isomerized aliphatic hydrocarbon, branched chain aliphatic hydrocarbons, aromatic hydrocarbons, and combinations thereof.
  • liquid carriers examples include, but are not limited to, aliphatic hydrocarbons, isoparaffinic compounds, paraffinic compounds, dearomatized hydrocarbon compounds, and the like.
  • the liquid carriers can include, but are not limited to, Isopar-GTM, Isopar-HTM, Isopar-LTM, Isopar-MTM, Isopar-KTM, Isopar-VTM, Norpar 12TM, Norpar 13TM, Norpar 15TM, Exxol D40TM, Exxol D80TM, Exxol D100TM, Exxol D130TM, and Exxol D140TM (each sold by EXXON CORPORATION); Teclen N-16TM, Teclen N-20TM, Teclen N-22TM, Nisseki Naphthesol LTM, Nisseki Naphthesol MTM, Nisseki Naphthesol HTM, #0 Solvent LTM, #0 Solvent MTM, #0 Solvent HTM, Nisse
  • the liquid carrier can constitute about 20% to 99.5% by weight of the electrostatic ink composition, in some examples 50% to 99.5% by weight of the electrostatic ink composition.
  • the liquid carrier may constitute about 40 to 90 % by weight of the electrostatic ink composition.
  • the liquid carrier may constitute about 60% to 80% by weight of the electrostatic ink composition.
  • the liquid carrier may constitute about 90% to 99.5% by weight of the electrostatic ink composition, in some examples 95% to 99% by weight of the electrostatic ink composition.
  • the electrostatic ink composition when printed on a print substrate, may be substantially free from liquid carrier.
  • the liquid carrier may be removed, e.g. by an electrophoresis processes during printing and/or evaporation, such that substantially just solids are transferred to the print substrate.
  • Substantially free from liquid carrier may indicate that the ink printed on the print substrate contains less than 5 wt% liquid carrier, in some examples, less than 2 wt% liquid carrier, in some examples less than 1 wt% liquid carrier, in some examples less than 0.5 wt% liquid carrier.
  • the ink printed on the print substrate is free from liquid carrier.
  • the method involves using and/or the electrostatic ink composition includes a resin, which may be a thermoplastic resin.
  • a thermoplastic polymer is sometimes referred to as a thermoplastic resin.
  • the resin may coat a pigment, e.g. the cyan pigment, such that the particles include a core of pigment, and have an outer layer of resin thereon.
  • the outer layer of resin may coat the pigment partially or completely.
  • the resin includes a polymer.
  • the polymer of the resin may be selected from ethylene or propylene acrylic acid co-polymers; ethylene or propylene methacrylic acid co-polymers; co-polymers of ethylene or propylene (e.g. 80 wt% to 99.9 wt%), and alkyl (e.g. C1 to C5) ester of methacrylic or acrylic acid (e.g. 0.1 wt% to 20 wt%); co-polymers of ethylene (e.g. 80 wt% to 99.9 wt%), acrylic or methacrylic acid (e.g. 0.1 wt% to 20.0 wt%) and alkyl (e.g.
  • ester of methacrylic or acrylic acid e.g. 0.1 wt% to 20 wt%)
  • acrylic resins e.g. co-polymer of acrylic or methacrylic acid and at least one alkyl ester of acrylic or methacrylic acid wherein alkyl may have from 1 to about 20 carbon atoms, such as methyl methacrylate (e.g. 50% to 90%)/methacrylic acid (e.g. 0 wt% to 20 wt%)/ethylhexylacrylate (e.g. 10 wt% to 50 wt%)); ethylene-acrylic acid ionomers and combinations thereof.
  • the resin may further include other polymers, including, but not limited to, ethylene vinyl acetate co-polymers; co-polymers of ethylene or propylene (e.g. 70 wt% to 99.9 wt%) and maleic anhydride (e.g.
  • polyethylene polystyrene; isotactic polypropylene (crystalline); co-polymers of ethylene ethylene ethyl acrylate; polyesters; polyvinyl toluene; polyamides; styrene/butadiene co-polymers; epoxy resins; ethylene-acrylate terpolymers: ethylene-acrylic esters-maleic anhydride (MAH) or glycidyl methacrylate (GMA) terpolymers
  • the resin may include a polymer having acidic side groups.
  • the polymer having acidic side groups may have an acidity of 50 mg KOH/g or more, in some examples an acidity of 60 mg KOH/g or more, in some examples an acidity of 70 mg KOH/g or more, in some examples an acidity of 80 mg KOH/g or more, in some examples an acidity of 90 mg KOH/g or more, in some examples an acidity of 100 mg KOH/g or more, in some examples an acidity of 105 mg KOH/g or more, in some examples 110 mg KOH/g or more, in some examples 115 mg KOH/g or more.
  • the polymer having acidic side groups may have an acidity of 200 mg KOH/g or less, in some examples 190 mg or less, in some examples 180 mg or less, in some examples 130 mg KOH/g or less, in some examples 120 mg KOH/g or less.
  • Acidity of a polymer, as measured in mg KOH/g can be measured using standard procedures known in the art, for example using the procedure described in ASTM D1386.
  • the resin may include a polymer, in some examples a polymer having acidic side groups, that has a melt flow rate of less than about 70 g/10 minutes, in some examples about 60 g/10 minutes or less, in some examples about 50 g/10 minutes or less, in some examples about 40 g/10 minutes or less, in some examples 30 g/10 minutes or less, in some examples 20 g/10 minutes or less, in some examples 10 g/10 minutes or less.
  • all polymers having acidic side groups and/or ester groups in the particles each individually have a melt flow rate of less than 90 g/10 minutes, 80 g/10 minutes or less, in some examples 80 g/10 minutes or less, in some examples 70 g/10 minutes or less, in some examples 70 g/10 minutes or less, in some examples 60 g/10 minutes or less.
  • the polymer having acidic side groups can have a melt flow rate of about 10 g/10 minutes to about 120 g/10 minutes, in some examples about 10 g/10 minutes to about 70 g/10 minutes, in some examples about 10 g/10 minutes to 40 g/10 minutes, in some examples 20 g/10 minutes to 30 g/10 minutes.
  • the polymer having acidic side groups can have a melt flow rate of, in some examples, about 50 g/10 minutes to about 120 g/10 minutes, in some examples 60 g/10 minutes to about 100 g/10 minutes.
  • the melt flow rate can be measured using standard procedures known in the art, for example as described in ASTM D1238.
  • the acidic side groups may be in free acid form or may be in the form of an anion and associated with one or more counterions, typically metal counterions, e.g. a metal selected from the alkali metals, such as lithium, sodium and potassium, alkali earth metals, such as magnesium or calcium, and transition metals, such as zinc.
  • the polymer having acidic sides groups can be selected from resins such as co-polymers of ethylene and an ethylenically unsaturated acid of either acrylic acid or methacrylic acid; and ionomers thereof, such as methacrylic acid and ethylene-acrylic or methacrylic acid co-polymers which are at least partially neutralized with metal ions (e.g.
  • the polymer including acidic side groups can be a co-polymer of ethylene and an ethylenically unsaturated acid of either acrylic or methacrylic acid, where the ethylenically unsaturated acid of either acrylic or methacrylic acid constitute from 5 wt% to about 25 wt% of the co-polymer, in some examples from 10 wt% to about 20 wt% of the co-polymer.
  • the resin may include two different polymers having acidic side groups.
  • the two polymers having acidic side groups may have different acidities, which may fall within the ranges mentioned above.
  • the resin may include a first polymer having acidic side groups that has an acidity of from 10 mg KOH/g to 110 mg KOH/g, in some examples 20 mg KOH/g to 110 mg KOH/g, in some examples 30 mg KOH/g to 110 mg KOH/g, in some examples 50 mg KOH/g to 110 mg KOH/g, and a second polymer having acidic side groups that has an acidity of 110 mg KOH/g to 130 mg KOH/g.
  • the resin may include two different polymers having acidic side groups: a first polymer having acidic side groups that has a melt flow rate of about 10 g/10 minutes to about 50 g/10 minutes and an acidity of from 10 mg KOH/g to 110 mg KOH/g, in some examples 20 mg KOH/g to 110 mg KOH/g, in some examples 30 mg KOH/g to 110 mg KOH/g,in some examples 50 mg KOH/g to 110 mg KOH/g, and a second polymer having acidic side groups that has a melt flow rate of about 50 g/10 minutes to about 120 g/10 minutes and an acidity of 110 mg KOH/g to 130 mg KOH/g.
  • the first and second polymers may be absent of ester groups.
  • the ratio of the first polymer having acidic side groups to the second polymer having acidic side groups can be from about 10:1 to about 2:1.
  • the ratio can be from about 6:1 to about 3:1, in some examples about 4:1.
  • the resin may include a polymer having a melt viscosity of 15000 poise or less, in some examples a melt viscosity of 10000 poise or less, in some examples 1000 poise or less, in some examples 100 poise or less, in some examples 50 poise or less, in some examples 10 poise or less; said polymer may be a polymer having acidic side groups as described herein.
  • the resin may include a first polymer having a melt viscosity of 15000 poise or more, in some examples 20000 poise or more, in some examples 50000 poise or more, in some examples 70000 poise or more; and in some examples, the resin may include a second polymer having a melt viscosity less than the first polymer, in some examples a melt viscosity of 15000 poise or less, in some examples a melt viscosity of 10000 poise or less, in some examples 1000 poise or less, in some examples 100 poise or less, in some examples 50 poise or less, in some examples 10 poise or less.
  • the resin may include a first polymer having a melt viscosity of more than 60000 poise, in some examples from 60000 poise to 100000 poise, in some examples from 65000 poise to 85000 poise; a second polymer having a melt viscosity of from 15000 poise to 40000 poise, in some examples 20000 poise to 30000 poise, and a third polymer having a melt viscosity of 15000 poise or less, in some examples a melt viscosity of 10000 poise or less, in some examples 1000 poise or less, in some examples 100 poise or less, in some examples 50 poise or less, in some examples 10 poise or less; an example of the first polymer is Nucrel 960 (from DuPont), and example of the second polymer is Nucrel 699 (from DuPont), and an example of the third polymer is AC-5120 or AC-5180 (from Honeywell).
  • the first, second and third polymers may be polymers having acidic side groups as described herein.
  • the melt viscosity can be measured using a rheometer, e.g. a commercially available AR-2000 Rheometer from Thermal Analysis Instruments, using the geometry of: 25mm steel plate-standard steel parallel plate, and finding the plate over plate rheometry isotherm at 120°C, 0.01 hz shear rate.
  • the polymer (excluding any other components of the electrostatic ink composition) may have a melt viscosity of 6000 poise or more, in some examples a melt viscosity of 8000 poise or more, in some examples a melt viscosity of 10000 poise or more, in some examples a melt viscosity of 12000 poise or more.
  • the resin includes a plurality of polymers all the polymers of the resin may together form a mixture (excluding any other components of the electrostatic ink composition) that has a melt viscosity of 6000 poise or more, in some examples a melt viscosity of 8000 poise or more, in some examples a melt viscosity of 10000 poise or more, in some examples a melt viscosity of 12000 poise or more.
  • Melt viscosity can be measured using standard techniques. The melt viscosity can be measured using a rheometer, e.g. a commercially available AR-2000 Rheometer from Thermal Analysis Instruments, using the geometry of: 25mm steel plate-standard steel parallel plate, and finding the plate over plate rheometry isotherm at 120°C, 0.01 hz shear rate.
  • the resin may include two different polymers having acidic side groups that are selected from co-polymers of ethylene and an ethylenically unsaturated acid of either acrylic acid or methacrylic acid; or ionomers thereof, such as methacrylic acid and ethylene-acrylic or methacrylic acid co-polymers which are at least partially neutralized with metal ions (e.g. Zn, Na, Li) such as SURLYN® ionomers.
  • metal ions e.g. Zn, Na, Li
  • the resin may include (i) a first polymer that is a co-polymer of ethylene and an ethylenically unsaturated acid of either acrylic acid and methacrylic acid, wherein the ethylenically unsaturated acid of either acrylic or methacrylic acid constitutes from 8 wt% to about 16 wt% of the co-polymer, in some examples 10 wt% to 16 wt% of the co-polymer; and (ii) a second polymer that is a co-polymer of ethylene and an ethylenically unsaturated acid of either acrylic acid and methacrylic acid, wherein the ethylenically unsaturated acid of either acrylic or methacrylic acid constitutes from 12 wt% to about 30 wt% of the co-polymer, in some examples from 14 wt% to about 20 wt% of the co-polymer, in some examples from 16 wt% to about 20 wt% of the co-poly
  • the resin may include a polymer having acidic side groups, as described above (which may be free of ester side groups), and a polymer having ester side groups.
  • the polymer having ester side groups may be a thermoplastic polymer.
  • the polymer having ester side groups may further include acidic side groups.
  • the polymer having ester side groups may be a co-polymer of a monomer having ester side groups and a monomer having acidic side groups.
  • the polymer may be a co-polymer of a monomer having ester side groups, a monomer having acidic side groups, and a monomer absent of any acidic and ester side groups.
  • the monomer having ester side groups may be a monomer selected from esterified acrylic acid or esterified methacrylic acid.
  • the monomer having acidic side groups may be a monomer selected from acrylic or methacrylic acid.
  • the monomer absent of any acidic and ester side groups may be an alkylene monomer, including, but not limited to, ethylene or propylene.
  • the esterified acrylic acid or esterified methacrylic acid may, respectively, be an alkyl ester of acrylic acid or an alkyl ester of methacrylic acid.
  • the alkyl group in the alkyl ester of acrylic or methacrylic acid may be an alkyl group having 1 to 30 carbons, in some examples 1 to 20 carbons, in some examples 1 to 10 carbons; in some examples selected from methyl, ethyl, iso-propyl, n-propyl, t-butyl, iso-butyl, n-butyl and pentyl.
  • the polymer having ester side groups may be a co-polymer of a first monomer having ester side groups, a second monomer having acidic side groups and a third monomer which is an alkylene monomer absent of any acidic and ester side groups.
  • the polymer having ester side groups may be a co-polymer of (i) a first monomer having ester side groups selected from esterified acrylic acid or esterified methacrylic acid, in some examples an alkyl ester of acrylic or methacrylic acid, (ii) a second monomer having acidic side groups selected from acrylic or methacrylic acid and (iii) a third monomer which is an alkylene monomer selected from ethylene and propylene.
  • the first monomer may constitute 1% to 50% by weight of the co-polymer, in some examples 5% to 40% by weight, in some examples 5% to 20% by weight of the co-polymer, in some examples 5% to 15% by weight of the co-polymer.
  • the second monomer may constitute 1% to 50 % by weight of the co-polymer, in some examples 5% to 40% by weight of the co-polymer, in some examples 5% to 20% by weight of the co-polymer, in some examples 5% to 15% by weight of the co-polymer.
  • the first monomer can constitute 5% to 40 % by weight of the co-polymer, the second monomer constitutes 5% to 40% by weight of the co-polymer, and with the third monomer constituting the remaining weight of the co-polymer. In some examples, the first monomer constitutes 5% to 15% by weight of the co-polymer, the second monomer constitutes 5% to 15% by weight of the co-polymer, with the third monomer constituting the remaining weight of the co-polymer. In some examples, the first monomer constitutes 8% to 12% by weight of the co-polymer, the second monomer constitutes 8% to 12% by weight of the co-polymer, with the third monomer constituting the remaining weight of the co-polymer.
  • the first monomer constitutes about 10% by weight of the co-polymer
  • the second monomer constitutes about 10% by weight of the co-polymer
  • with the third monomer constituting the remaining weight of the co-polymer.
  • the polymer may be selected from the Bynel® class of monomer, including Bynel 2022 and Bynel 2002, which are available from DuPont®.
  • the polymer having ester side groups may constitute 1% or more by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in the electrostatic ink composition and/or the ink printed on the print substrate, e.g. the total amount of the polymer or polymers having acidic side groups and polymer having ester side groups.
  • the polymer having ester side groups may constitute 5% or more by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in some examples 8% or more by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in some examples 10% or more by weight of the total amount of the resin polymers, e.g.
  • thermoplastic resin polymers in some examples 15% or more by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in some examples 20% or more by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in some examples 25% or more by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in some examples 30% or more by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in some examples 35% or more by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in the electrostatic ink composition and/or the ink printed on the print substrate.
  • the polymer having ester side groups may constitute from 5% to 50% by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in the electrostatic ink composition and/or the ink printed on the print substrate, in some examples 10% to 40% by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in the electrostatic ink composition and/or the ink printed on the print substrate, in some examples 5% to 30% by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in the electrostatic ink composition and/or the ink printed on the print substrate, in some examples 5% to 15% by weight of the total amount of the resin polymers, e.g.
  • thermoplastic resin polymers in the electrostatic ink composition and/or the ink printed on the print substrate in some examples 15% to 30% by weight of the total amount of the resin polymers, e.g. thermoplastic resin polymers, in the electrostatic ink composition and/or the ink printed on the print substrate.
  • the polymer having ester side groups may have an acidity of 50 mg KOH/g or more, in some examples an acidity of 60 mg KOH/g or more, in some examples an acidity of 70 mg KOH/g or more, in some examples an acidity of 80 mg KOH/g or more.
  • the polymer having ester side groups may have an acidity of 100 mg KOH/g or less, in some examples 90 mg KOH/g or less.
  • the polymer having ester side groups may have an acidity of 60 mg KOH/g to 90 mg KOH/g, in some examples 70 mg KOH/g to 80 mg KOH/g.
  • the polymer having ester side groups may have a melt flow rate of about 10 g/10 minutes to about 120 g/10 minutes, in some examples about 10 g/10 minutes to about 50 g/10 minutes, in some examples about 20 g/10 minutes to about 40 g/10 minutes, in some examples about 25 g/10 minutes to about 35 g/10 minutes.
  • the polymer, polymers, co-polymer or co-polymers of the resin can in some examples be selected from the Nucrel family of toners (e.g. Nucrel 403TM, Nucrel 407TM, Nucrel 609HSTM, Nucrel 908HSTM, Nucrel 1202HCTM, Nucrel 30707TM, Nucrel 1214TM, Nucrel 903TM, Nucrel 3990TM, Nucrel 910TM, Nucrel 925TM, Nucrel 699TM, Nucrel 599TM, Nucrel 960TM, Nucrel RX 76TM, Nucrel 2806TM, Bynell 2002, Bynell 2014, and Bynell 2020 (sold by E. I.
  • the Aclyn family of toners e.g. Aclyn 201 , Aclyn 246, Aclyn 285, and Aclyn 295
  • the Lotader family of toners e.g. Lotader 2210, Lotader, 3430, and Lotader 8200 (sold by Arkema)
  • the pigment constitutes a certain wt%, e.g. from 1 wt%, to 30 wt% of the solids of the electrostatic ink composition, and the remaining wt% of the solids of the electrostatic ink composition is formed by the resin and, in some examples, any other additives that are present.
  • the other additives may constitute 10 wt% or less of the solids of the electrostatic ink composition, in some examples 5wt% or less of the solids of the electrostatic ink composition, in some examples 3 wt% or less of the solids of the electrostatic ink composition.
  • the resin may constitute 5% to 99 % by weight of the solids in the electrostatic ink composition, in some examples 50 % to 90 % by weight of the solids of the electrostatic ink composition, in some examples 70 % to 90 % by weight of the solids of the electrostatic ink composition.
  • the remaining wt % of the solids in the ink composition may be a pigment and, in some examples, any other additives that may be present.
  • the method involves using and/or the electrostatic ink composition includes a charge director.
  • the charge director may be added in order to impart and/or maintain sufficient electrostatic charge on the ink particles, which may be particles comprising the pigment, the resin, the dispersant and phthalocyanine having acid groups.
  • the charge director may be selected from ionic compounds, such as metal salts of fatty acids, metal salts of sulfo-succinates, metal salts of oxyphosphates, metal salts of alkyl-benzenesulfonic acid, metal salts of aromatic carboxylic acids or sulfonic acids, as well as zwitterionic and non-ionic compounds, such as polyoxyethylated alkylamines, lecithin, polyvinylpyrrolidone, organic acid esters of polyvalent alcohols, etc.
  • the charge director is selected from, but is not limited to, oil-soluble petroleum sulfonates (e.g.
  • sulfonic acid salts including, but not limited to, barium, sodium, calcium, and aluminum salts of a sulfonic acid.
  • the sulfonic acids may include, but are not limited to, alkyl sulfonic acids, aryl sulfonic acids, and sulfonic acids of alkyl succinates (e.g. see WO 2007/130069 ).
  • the charge director imparts a negative charge on the particles of the ink composition. In some examples, the charge director imparts a positive charge on the particles of the ink composition. In some examples, the charge director comprises a phospholipid, in some examples a salt or an alcohol of a phospholipid. In some examples, the charge director comprises species selected from a phosphatidylcholine and derivatives thereof.
  • the charge director includes a sulfosuccinate moiety of the general formula [R x -O-C(O)CH 2 CH(SO 3 - )C(O)-O-R y ], where each of R x and R y is an alkyl group.
  • the charge director includes nanoparticles of a simple salt and a sulfosuccinate salt of the general formula MAn, wherein M is a metal, n is the valence of M, and A is an ion of the general formula [R x -O-C(O)CH 2 CH(SO 3 - )C(O)-O-R y ], where each of R x and R y is an alkyl group, or other charge directors as found in WO2007130069 (wherein R x and R y in this application correspond, respectively, to R 1 and R 2 in WO2007130069 ), which is incorporation herein by reference in its entirety.
  • the sulfosuccinate salt of the general formula MAn is an example of a micelle forming salt.
  • the charge director may be substantially free or free of an acid of the general formula HA, where A is as described above.
  • the charge director may include micelles of said sulfosuccinate salt enclosing at least some of the nanoparticles.
  • the charge director may include at least some nanoparticles having a size of 200 nm or less, and/or in some examples 2 nm or more.
  • simple salts are salts that do not form micelles by themselves, although they may form a core for micelles with a micelle forming salt.
  • the ions constructing the simple salts are all hydrophilic.
  • the simple salt may include a cation selected from the group consisting of Mg , Ca , Ba , NH4 , tert-butyl ammonium, Li+, and AI+3, or from any sub-group thereof.
  • the simple salt may include an anion selected from the group consisting of SO 4 2- , PO 3- , NO 3- , HPO 4 2- , CO 3 2- , acetate, trifluoroacetate (TFA), Cl - , BF 4 - , F-, CI0 4 -, and TiO 3 4- , or from any sub-group thereof.
  • the simple salt may be selected from CaCO 3 , Ba 2 TiO 3 , Al 2 (SO 4 ), Al(NO 3 ) 3 , Ca 3 (PO 4 ) 2 , BaSO 4 , BaHPO 4 , Ba 2 (PO 4 ) 3 , CaSO 4 , (NH 4 ) 2 CO 3 , (NH 4 ) 2 SO 4 , NH 4 OAc, Tert- butyl ammonium bromide, NH 4 NO 3 , LiTFA, Al 2 (SO 4 )3, LiClO 4 and LiBF 4 , or any sub-group thereof.
  • the charge director may further include basic barium petronate (BBP).
  • each of R x and R y is an aliphatic alkyl group.
  • each of R x and R y independently is a C6-25 alkyl.
  • said aliphatic alkyl group is linear.
  • said aliphatic alkyl group is branched.
  • said aliphatic alkyl group includes a linear chain of more than 6 carbon atoms.
  • R x and R y are the same. In some examples, at least one of R x and R y is C13H27.
  • M is Na, K, Cs, Ca, or Ba.
  • the formula [R x -O-C(O)CH 2 CH(SO 3 - )C(O)-O-R y ] and/or the formula MAn may be as defined in any part of WO2007130069 (wherein R x and R y in this application correspond, respectively, to R 1 and R 2 in WO2007130069 ).
  • the charge director may include one of, some of or all of (i) soya lecithin, (ii) a barium sulfonate salt, such as basic barium petronate (BPP), and (iii) an isopropyl amine sulfonate salt.
  • BPP basic barium petronate
  • An example isopropyl amine sulphonate salt is dodecyl benzene sulfonic acid isopropyl amine, which is available from Croda.
  • the charge director constitutes about 0.001% to 20%, in some examples 0.01 % to 20% by weight, in some examples 0.01 to 10% by weight, in some examples 0.01 % to 1% by weight of the solids of an electrostatic ink composition. In some examples, the charge director constitutes about 0.001 % to 0.15 % by weight of the solids of the electrostatic ink composition, in some examples 0.001 % to 0.15 %, in some examples 0.001 % to 0.02 % by weight of the solids of an electrostatic ink composition, in some examples 0.1 % to 2 % by weight of the solids of the electrostatic ink composition, in some examples 0.2 % to 1.5 % by weight of the solids of the electrostatic ink composition in some examples 0.1 % to 1 % by weight of the solids of the electrostatic ink composition, in some examples 0.2 % to 0.8 % by weight of the solids of the electrostatic ink composition.
  • the charge director is present in an amount of at least 1 mg of charge director per gram of solids of the electrostatic ink composition (which will be abbreviated to mg/g), in some examples at least 2 mg/g, in some examples at least 3 mg/g, in some examples at least 4 mg/g, in some examples at least 5 mg/g.
  • the moderate acid is present in the amounts stated above, and the charge director is present in an amount of from 1 mg to 50 mg of charge director per gram of solids of the electrostatic ink composition (which will be abbreviated to mg/g), in some examples from 1 mg/g to 25 mg/g, in some examples from 1 mg/g to 20 mg/g, in some examples from 1 mg/g to 15 mg/g, in some examples from 1 mg/g to 10 mg/g, in some examples from 3 mg/g to 20 mg/g, in some examples from 3 mg/g to 15 mg/g, in some examples from 5 mg/g to 10 mg/g.
  • mg/g 1 mg/g to 50 mg of charge director per gram of solids of the electrostatic ink composition
  • the electrostatic ink composition may include a charge adjuvant.
  • a charge adjuvant may promote charging of the particles when a charge director is present.
  • the method as described here may involve adding a charge adjuvant at any stage.
  • the charge adjuvant can include, but is not limited to, barium petronate, calcium petronate, Co salts of naphthenic acid, Ca salts of naphthenic acid, Cu salts of naphthenic acid, Mn salts of naphthenic acid, Ni salts of naphthenic acid, Zn salts of naphthenic acid, Fe salts of naphthenic acid, Ba salts of stearic acid, Co salts of stearic acid, Pb salts of stearic acid, Zn salts of stearic acid, Al salts of stearic acid, Zn salts of stearic acid, Cu salts of stearic acid, Pb salts of stearic acid, Fe salts of stearic acid, metal carboxylates
  • the charge adjuvant is or includes aluminum di- or tristearate.
  • the charge adjuvant may be present in an amount of about 0.1 to 5 % by weight, in some examples about 0.1 to 1 % by weight, in some examples about 0.3 to 0.8 % by weight of the solids of the electrostatic ink composition, , in some examples about 1 wt % to 3 wt% of the solids of the electrostatic ink composition, in some examples about 1.5 wt % to 2.5 wt% of the solids of the electrostatic ink composition.
  • the electrostatic ink composition further includes, e.g. as a charge adjuvant, a salt of multivalent cation and a fatty acid anion.
  • the salt of multivalent cation and a fatty acid anion can act as a charge adjuvant.
  • the multivalent cation may, in some examples, be a divalent or a trivalent cation.
  • the multivalent cation is selected from Group 2, transition metals and Group 3 and Group 4 in the Periodic Table.
  • the multivalent cation includes a metal selected from Ca, Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Al and Pb.
  • the multivalent cation is Al3+.
  • the fatty acid anion may be selected from a saturated or unsaturated fatty acid anion.
  • the fatty acid anion may be selected from a C 8 to C 26 fatty acid anion, in some examples a C 14 to C 22 fatty acid anion, in some examples a C 16 to C 20 fatty acid anion, in some examples a C 17 , C 18 or C 19 fatty acid anion.
  • the fatty acid anion is selected from a caprylic acid anion, capric acid anion, lauric acid anion, myristic acid anion, palmitic acid anion, stearic acid anion, arachidic acid anion, behenic acid anion and cerotic acid anion.
  • the charge adjuvant which may, for example, be or include a salt of multivalent cation and a fatty acid anion, may be present in an amount of 0.1 wt% to 5 wt% of the solids of the electrostatic ink composition, in some examples in an amount of 0.1 wt% to 2 wt% of the solids of the electrostatic ink composition, in some examples in an amount of 0.1 wt% to 2 wt% of the solids of the electrostatic ink composition, in some examples in an amount of 0.3 wt% to 1.5 wt% of the solids of the electrostatic ink composition, in some examples about 0.5 wt% to 1.2 wt% of the solids of the electrostatic ink composition, in some examples about 0.8 wt% to 1 wt% of the solids of the electrostatic ink composition, in some examples about 1 wt % to 3 wt% of the solids of the electrostatic ink composition, in some examples about 1.5 wt % to 2.5
  • the electrostatic ink composition may include an additive or a plurality of additives.
  • the additive or plurality of additives may be added at any stage of the method.
  • the additive or plurality of additives may be selected from a wax, a surfactant, biocides, organic solvents, viscosity modifiers, materials for pH adjustment, sequestering agents, preservatives, compatibility additives, emulsifiers and the like.
  • the wax may be an incompatible wax.
  • incompatible wax may refer to a wax that is incompatible with the resin. Specifically, the wax phase separates from the resin phase upon the cooling of the resin fused mixture on a print substrate during and after the transfer of the ink film to the print substrate, e.g. from an intermediate transfer member, which may be a heated blanket.
  • a method of producing a cyan electrostatic ink composition comprising: combining a cyan pigment, a basic dispersant and a phthalocyanine having acid groups, a resin, and a charge director to form the electrostatic ink composition.
  • the method comprises mixing the cyan pigment, the dispersant and the phthalocyanine having acid groups to form a pigment dispersion; and then adding the resin to the pigment dispersion and grinding the pigment dispersion with the resin, and wherein a charge director is combined with the pigment, dispersant and the phthalocyanine having acid groups before, during or after the grinding of the pigment dispersion with the resin, to form the electrostatic ink composition.
  • the mixing of the pigment, dispersant and phthalocyanine having acid groups to form a pigment dispersion comprises grinding the pigment, the dispersant and the phthalocyanine having acid groups together.
  • the grinding of the pigment and dispersant to form a pigment dispersion comprises grinding the pigment, the dispersant and the phthalocyanine having acid groups and a liquid carrier.
  • this liquid carrier is termed a first liquid carrier, and wherein the grinding the pigment dispersion with a resin comprises grinding the pigment dispersion with a resin and a second liquid carrier.
  • the first liquid carrier and the second liquid carrier are the same.
  • a method of producing an electrostatic ink composition comprising:
  • the method of forming an electrostatic ink composition includes:
  • the method of forming an electrostatic ink composition includes:
  • the method of forming an electrostatic ink composition includes:
  • the method of forming an electrostatic ink composition includes:
  • the method of forming an electrostatic ink composition includes:
  • the method of forming an electrostatic ink composition includes:
  • the method of forming an electrostatic ink composition includes:
  • the method of forming an electrostatic ink composition includes:
  • the first liquid carrier and the second liquid carrier can be the same or different liquid carriers, and may be as described herein.
  • the second liquid carrier is added to the pigment dispersion after the pigment dispersion is formed, and then the pigment dispersion, the resin and the second liquid carrier are ground together.
  • the second liquid carrier can be a further volume of the first liquid carrier.
  • the pigment dispersion may lack the second liquid carrier.
  • the charge director is combined with the cyan pigment, the basic dispersant and the phthalocyanine having acid groups before, during or after the grinding of the pigment dispersion with the resin to form the electrostatic ink composition
  • the charge director is combined with the cyan pigment and basic dispersant after the grinding of the pigment dispersion with the resin, and, if present, the first liquid carrier, to form the electrostatic ink composition.
  • mixing components together may also involve grinding, e.g. milling, components together.
  • grinding of either or both steps i.e. mixing the cyan pigment, the basic dispersant and phthalocyanine having acid groups to form the pigment dispersion or grinding the pigment dispersion with the resin
  • a ball mill e.g. an agitated small media mill.
  • the grinding of either or both steps takes place in a ball mill for at least 15 minutes, in some examples at least 30 minutes, in some examples 30 minutes to 15 hours, in some examples 30 minutes to 10 hours, in some examples 30 minutes to 10 hours, in some examples 30 minutes to 5 hours, and/or in some examples the ball mill rotates at an rpm of at least 100 rpm, in some examples an rpm of at least 500 rpm, in some examples an rpm of 100 rpm to 6000 rpm, in some examples an rpm of 1000 rpm to 6000 rpm.
  • the balls used in a ball mill may be, for example, metal, e.g.
  • the cyan pigment may be a particulate pigment. If the cyan pigment is a particulate pigment, grinding of the pigment may indicate that at least some of the particles of the pigment are reduced in size. Grinding of the pigment dispersion may involve reduction in size of at least some of the particles in the pigment dispersion, which may comprise the cyan pigment and the resin.
  • the surface on which the (latent) electrostatic image is formed or developed may be on a rotating member, e.g. in the form of a cylinder.
  • the surface on which the (latent) electrostatic image is formed or developed may form part of a photo imaging plate (PIP).
  • the method may involve passing the electrostatic ink composition between a stationary electrode and a rotating member, which may be a member having the surface having the (latent) electrostatic image thereon or a member in contact with the surface having the (latent) electrostatic image thereon.
  • a voltage is applied between the stationary electrode and the rotating member, such that particles adhere to the surface of the rotating member.
  • the intermediate transfer member if present, may be a rotating flexible member, which may be heated, e.g. to a temperature of from 80 to 160 °C.
  • the present disclosure also provides an electrostatic ink composition producible according to the method described herein. There may also be provided a print substrate having printed thereon an electrostatic ink composition producible according to the method described herein.
  • the print substrate may be any suitable substrate.
  • the substrate may be any suitable substrate capable of having an image printed thereon.
  • the substrate may include a material selected from an organic or inorganic material.
  • the material may include a natural polymeric material, e.g. cellulose.
  • the material may include a synthetic polymeric material, e.g. a polymer formed from alkylene monomers, including, but not limited to, polyethylene and polypropylene, and co-polymers such as styrene-polybutadiene.
  • the polypropylene may, in some examples, be biaxially orientated polypropylene.
  • the material may include a metal, which may be in sheet form.
  • the metal may be selected from or made from, for instance, aluminium (Al), silver (Ag), tin (Sn), copper (Cu), mixtures thereof.
  • the substrate includes a cellulosic paper.
  • the cellulosic paper is coated with a polymeric material, e.g. a polymer formed from styrene-butadiene resin.
  • the cellulosic paper has an inorganic material bound to its surface (before printing with ink) with a polymeric material, wherein the inorganic material may be selected from, for example, kaolinite or calcium carbonate.
  • the substrate is, in some examples, a cellulosic print substrate such as paper.
  • the cellulosic print substrate is, in some examples, a coated cellulosic print.
  • a primer may be coated onto the print substrate, before the electrostatic ink composition is printed onto the print substrate.
  • 'Isopar' is IsoparTM L Fluid, produced by ExxonMobil and having CAS Number 64742-48-9.
  • Cyan main pigment is Lionol Blue FG-7351, available from TOYO Company.
  • Figures 1 and 2 display a scanning electron micrograph which shows that these cyan pigments are either spherical or ellipsoidal and many times have well defined facets.
  • the secondary pigment for Cyan is Heliogen Green D 8730, produced by BASF.
  • the 'Resins' used in the Examples were Nucrel 699, available from DuPont, and A-C 5120, available from Honeywell, in the weight ratio of 4:1.
  • the additives used in the above are VCA, DS72 and HPB.
  • VCA indicates an aluminium tristearate and palmitate salt, available from Sigma Aldrich.
  • HPB indicates an homopolymer polyethylene wax, available under the trade name Acumist B6 from Honeywell company.
  • DS72 is a silica powder, available under the trade name Aerosil R 7200 from Degussa-Evonik.
  • SCD is synthetic charge director, being a barium bis sulfosuccinate salt as described in US 2009/0311614 or WO2007130069 , supplied by Hewlett-Packard Indigo.
  • dispersants shown in Table 1 and 2 were used. when table 1 indicates the dispersants which were used in the initial development stage of dispersant screening .
  • the dispersants and synergist shown in table 2 are used and referred to, where % AOWP is the Percentage Agent on the Weight of Pigment and DMA is the Developed Mass per Area.
  • Electroink solutions were produced using a lab grinding tool called attritor S1, formulation comprising 10-20 wt% Cyan pigments, 60-70 wt% resin, VCA 1-5 wt%,HPB 1-5 wt% DS72 1-5 wt% and 15-20 wt% of Iso Par-L.
  • the dispersions were ground using the agitated small media mill having a ceramic bead media size of 0.6mm called Eiger (model M100) for 1-3 hrs. hours at approximately 4000 rpm and at a temperature of 20°C.
  • Eiger model M100
  • a pigment dispersion was prepared by grinding a formulation comprising 10-20 wt% Cyan pigment, 2-4 wt% liquid dispersant Lubrizol J560,1-3% Synergist SP5000 and 76-88 wt% Isopar -L in in the manner of Example 2.
  • An electroink was then prepared from the pigment dispersion by grinding 400-600 gr of the pigment dispersion with 1000-1500 gr of Resin and 200-500 gr of Isopar -L with 10-20 gr of VCA ,10-20 gr of HPB and 5-10 gr of DS72 in the manner of Example 1 to form a working electroink .
  • the general procedure for producing 4.5 HP Electroink is described in various patent applications such as in WO2013044991 , Example 1.
  • the pigment dispersion made in the previous step was used in place of the undispersed pigment used in the general method.
  • An electroink was prepared according to method of Example 3, except that the dispersant K500 at 20% AOWP was used in place of J560.
  • An electroink was prepared according to method of Example 3, except that the dispersant Lubrizol 2153 was used in place of Lubrizol K500.
  • An electroink was prepared according to method of Example 3, except that the dispersant Lubrizol 2153 was used in place of Lubrizol K500. And the pigment loading was increased in 5-10% as compare to reference (Example 1)
  • the working electroinks of Examples 1,3-5 composition is prepared in accordance with one of the Examples above.
  • a color adjust is done in order to write the down the developing voltage, verifying the OD is at the specification window.
  • verifying the OD is at the specification window.
  • a reference sample (example 1).
  • the goal for the test is to examine whether ink based on pigment dispersion reduce DMA.
  • Test configuration of this test is - Developer voltage of 450V ⁇ 30V, with high pressure in the first transfer. Then 16 separation from each of the examples describe above are printed in 4 different set point of OD (1.35, 1.4, 1.45, 1.5).

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Claims (13)

  1. Composition d'encre cyan électrostatique, la composition d'encre cyan électrostatique comprenant :
    un pigment cyan,
    un dispersant basique,
    une phtalocyanine ayant des groupes acides de formule (I)
    Figure imgb0011
     dans laquelle R1, R2, R3, R4, R1', R2', R3', R4', R1', R2", R3", R4", R1"', R2"', R3"', R4"', sont chacun indépendamment choisis parmi H et un groupe acide, avec au moins l'un de R1, R2, R3, R4, R1', R2', R3', R4' R1", R2", R3", R4", R1"', R2"', R3"', R4'" étant un groupe acide, une résine, et un directeur de charge, le pigment cyan étant un pigment de phtalocyanine, différent de la phtalocyanine ayant des groupes acides
  2. Composition d'encre cyan électrostatique selon la revendication 1, dans laquelle le pigment cyan est choisi parmi le pigment bleu 15:1, le pigment bleu 15:2, le pigment bleu 15:3, le pigment bleu 15:4, le pigment bleu 15:5, le pigment bleu 15:6, le pigment vert 7 et le pigment bleu 36.
  3. Composition d'encre cyan électrostatique selon la revendication 1, dans laquelle R1, R2, R3, R4, R1', R2', R3', R4', R1" R2", R3", R4", R1"', R2'" R3"', R4'" sont chacun indépendamment choisis parmi H et un groupe acide choisi parmi un groupe carboxyle et un groupe sulfate.
  4. Composition d'encre cyan électrostatique selon la revendication 1, dans laquelle R3, R3, R3" et R3'" sont chacun un groupe acide choisi parmi un groupe carboxyle et un groupe sulfate, et R1, R2, R4, R1', R2', R4, R1", R2", R4", R1"', R2"', R4'" sont chacun H.
  5. Composition d'encre cyan électrostatique selon la revendication 1, dans laquelle le rapport en poids du pigment cyan/phtalocyanine ayant des groupes acides est présent est de 50:1 à 1:1.
  6. Composition d'encre cyan électrostatique selon la revendication 1, dans laquelle le rapport en poids de pigment cyan/phtalocyanine ayant des groupes acides est présent est de 20:1 à 10:3.
  7. La composition d'encre cyan électrostatique selon la revendication 1, dans laquelle le dispersant basique a un indice de base total (TBN) d'au moins 5 mg de KOH / gr de matière.
  8. Composition d'encre cyan électrostatique selon la revendication 1, dans laquelle le dispersant est de formule (II)
    Figure imgb0012
     dans laquelle R1, R2 et R3 sont choisis parmi un groupe de tête contenant une amine, un groupe de queue d'hydrocarbure et d'hydrogène, au moins l'un de R1, R2 et R3 comprenant un groupe de queue d'hydrocarbure, et au moins l'un de R1, R2 et R3 comprend un groupe de tête contenant une amine.
  9. Composition d'encre cyan électrostatique selon la revendication 1, dans laquelle le dispersant comprend un ester d'acide ricinoléique, ou un dérivé de celui - ci.
  10. Procédé de production d'une composition d'encre électrostatique, le procédé comprenant :
    la combinaison d'un pigment cyan,
    d'un dispersant basique,
    d'une phtalocyanine ayant des groupes acides de formule (I),
    Figure imgb0013
     dans laquelle R1, R2, R3, R4, R1', R2', R3', R4' R1", R2", R3" , R4", R1"', R2"', R3"', R4'" sont chacun indépendamment choisis parmi H et un groupe acide, avec au moins l'un de R1, R2, R3, R4, R1', R2', R3', R4', R1", R2", R3", R4", R1"', R2"', R3"', R4'" étant un groupe acide, une résine et un directeur de charge pour former la composition d'encre électrostatique, le pigment cyan étant un pigment de phtalocyanine, différent de la phtalocyanine ayant des groupes acides.
  11. Procédé de production d'une composition d'encre cyan électrostatique selon la revendication 10, le procédé comprenant le mélange du pigment cyan, du dispersant et de la phtalocyanine ayant des groupes acides pour former une dispersion de pigment ; puis
    l'ajout de la résine à la dispersion de pigment et le broyage de la dispersion de pigment avec la résine, et dans lequel un directeur de charge est combiné avec le pigment, le dispersant et la phtalocyanine ayant des groupes acides avant, pendant ou après le broyage de la dispersion de pigment avec la résine, pour former la composition d'encre électrostatique.
  12. Procédé de production d'une composition d'encre cyan électrostatique selon la revendication 11, dans lequel le mélange du pigment, du dispersant et de la phtalocyanine ayant des groupes acides pour former une dispersion de pigment comprend le broyage du pigment, du dispersant, de la phthalocyanine ayant des groupes acides et un entraîneur liquide.
  13. Support d'impression sur lequel est imprimée une composition d'encre cyan électrostatique comprenant un pigment cyan, un dispersant basique, une phtalocyanine ayant des groupes acides de formule (I),
    Figure imgb0014
     dans laquelle R1, R2, R3, R4, R1', R2', R3', R4' R1", R2", R3", R4", R1"', R2"', R3"', R4'" sont chacun indépendamment sélectionnés parmi H et un groupe acide, avec au moins l'un de R1, R2, R3, R4, R1', R2', R3', R4' R1", R2", R3", R4", R1"', R2"', R3"', R4'" étant un groupe acide et une résine,
    le pigment cyan étant un pigment de phtalocyanine, différent de la phtalocyanine ayant des groupes acides.
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